Showing metabocard for Aminoadipic acid (MMDBc0000520)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-12-10 18:39:38 UTC
Update Date2024-04-30 19:32:46 UTC
Metabolite IDMMDBc0000520
Metabolite Identification
Common NameAminoadipic acid
DescriptionAminoadipic acid (CAS: 542-32-5), also known as 2-aminoadipate, is a metabolite in the principal biochemical pathway of lysine. It is an intermediate in the metabolism (i.e. breakdown or degradation) of lysine and saccharopine. It antagonizes neuroexcitatory activity modulated by the glutamate receptor N-methyl-D-aspartate (NMDA). Aminoadipic acid has also been shown to inhibit the production of kynurenic acid, a broad spectrum excitatory amino acid receptor antagonist, in brain tissue slices (PMID: 8566117 ). Recent studies have shown that aminoadipic acid is elevated in prostate biopsy tissues from prostate cancer patients (PMID: 23737455 ). Mutations in DHTKD1 (dehydrogenase E1 and transketolase domain-containing protein 1) have been shown to cause human 2-aminoadipic aciduria and 2-oxoadipic aciduria via impaired decarboxylation of 2-oxoadipate to glutaryl-CoA, which is the last step in the lysine degradation pathway (PMID: 23141293 ). Aging, diabetes, sepsis, and renal failure are known to catalyze the oxidation of lysyl residues to form 2-aminoadipic acid in human skin collagen and potentially other tissues (PMID: 18448817 ). Proteolytic breakdown of these tissues can lead to the release of free 2-aminoadipic acid. Studies in rats indicate that aminoadipic acid (along with the three branched-chain amino acids: leucine, valine, and isoleucine) levels are elevated in the pre-diabetic phase and so aminoadipic acid may serve as a predictive biomarker for the development of diabetes (PMID: 15389298 ). Long-term hyperglycemia of endothelial cells can also lead to elevated levels of aminoadipate which is thought to be a sign of lysine breakdown through oxidative stress and reactive oxygen species (ROS) (PMID: 21961526 ). 2-Aminoadipate is a potential small-molecule marker of oxidative stress (PMID: 21647514 ). Therefore, depending on the circumstances aminoadipic acid can act as an acidogen, a diabetogen, an atherogen, and a metabotoxin. An acidogen is an acidic compound that induces acidosis, which has multiple adverse effects on many organ systems. A diabetogen is a compound that can lead to type 2 diabetes. An atherogen is a compound that leads to atherosclerosis and cardiovascular disease. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of aminoadipic acid are associated with at least two inborn errors of metabolism including 2-aminoadipic aciduria and 2-oxoadipic aciduria. Aminoadipic acid is an organic acid and abnormally high levels of organic acids in the blood (organic acidemia), urine (organic aciduria), the brain, and other tissues lead to general metabolic acidosis. Acidosis typically occurs when arterial pH falls below 7.35. In infants with acidosis, the initial symptoms include poor feeding, vomiting, loss of appetite, weak muscle tone (hypotonia), and lack of energy (lethargy). These can progress to heart abnormalities, kidney abnormalities, liver damage, seizures, coma, and possibly death. These are also the characteristic symptoms of the untreated IEMs mentioned above. Many affected children with organic acidemias experience intellectual disability or delayed development. In adults, acidosis or acidemia is characterized by headaches, confusion, feeling tired, tremors, sleepiness, and seizures. As a diabetogen, serum aminoadipic levels appear to regulate glucose homeostasis and have been highly predictive of individuals who later develop diabetes (PMID: 24091325 ). In particular, aminoadipic acid lowers fasting plasma glucose levels and enhances insulin secretion from human islets. As an atherogen, aminoadipic acid has been found to be produced at high levels via protein lysine oxidation in atherosclerotic plaques (PMID: 28069522 ).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f922b796020>


  Mrv1652304222022262D          

 11 10  0  0  0  0            999 V2000
   -1.7862    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -0.2063    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3572    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862    1.0311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006   -0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -1.0311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006    0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -1.0311    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  7  2  0  0  0  0
  1  8  1  0  0  0  0
  6  9  2  0  0  0  0
  6 10  1  0  0  0  0
  2 11  1  6  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007f922b796020>

HMDB0000510
     RDKit          3D
Aminoadipic acid
 22 21  0  0  0  0  0  0  0  0999 V2000
   -1.9223    1.3023   -0.0400 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5601    0.0254   -0.6600 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2580   -0.4394    0.0101 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7537    0.6319   -0.2599 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1083    0.3953    0.3025 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8023   -0.8049   -0.1776 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2649   -1.5447   -1.0247 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0552   -1.1349    0.2969 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6486   -0.9418   -0.4803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5146   -2.0989   -0.9467 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8233   -0.6376    0.1828 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4790    2.1002   -0.5542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9609    1.3914   -0.1080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3285    0.2524   -1.7204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4545   -0.5633    1.1035 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0565   -1.4135   -0.3728 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7525    0.8370   -1.3467 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3535    1.5721    0.2166 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0591    0.4305    1.4101 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7272    1.2997    0.0228 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9000   -0.6112    0.0877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8834   -0.0483    1.0041 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  2  9  1  0
  9 10  2  0
  9 11  1  0
  1 12  1  0
  1 13  1  0
  2 14  1  6
  3 15  1  0
  3 16  1  0
  4 17  1  0
  4 18  1  0
  5 19  1  0
  5 20  1  0
  8 21  1  0
 11 22  1  0
M  END
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3D SDF for #<Metabolite:0x00007f922b796020>


  Mrv1652304222022262D          

 11 10  0  0  0  0            999 V2000
   -1.7862    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -0.2063    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3572    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862    1.0311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006   -0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -1.0311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006    0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -1.0311    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  7  2  0  0  0  0
  1  8  1  0  0  0  0
  6  9  2  0  0  0  0
  6 10  1  0  0  0  0
  2 11  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000520

> <DATABASE_NAME>
MIME

> <SMILES>
N[C@@H](CCCC(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H11NO4/c7-4(6(10)11)2-1-3-5(8)9/h4H,1-3,7H2,(H,8,9)(H,10,11)/t4-/m0/s1

> <INCHI_KEY>
OYIFNHCXNCRBQI-BYPYZUCNSA-N

> <FORMULA>
C6H11NO4

> <MOLECULAR_WEIGHT>
161.1558

> <EXACT_MASS>
161.068807845

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
15.528857992657501

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-aminohexanedioic acid

> <ALOGPS_LOGP>
-3.43

> <JCHEM_LOGP>
-2.799617140954382

> <ALOGPS_LOGS>
-0.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
4.417593887349678

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.014430671538277

> <JCHEM_PKA_STRONGEST_BASIC>
9.52703004922271

> <JCHEM_POLAR_SURFACE_AREA>
100.62

> <JCHEM_REFRACTIVITY>
35.8887

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.27e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
aminoadipate

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for #<Metabolite:0x00007f922b796020>

HMDB0000510
     RDKit          3D
Aminoadipic acid
 22 21  0  0  0  0  0  0  0  0999 V2000
   -1.9223    1.3023   -0.0400 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5601    0.0254   -0.6600 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2580   -0.4394    0.0101 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7537    0.6319   -0.2599 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1083    0.3953    0.3025 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8023   -0.8049   -0.1776 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2649   -1.5447   -1.0247 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0552   -1.1349    0.2969 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6486   -0.9418   -0.4803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5146   -2.0989   -0.9467 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8233   -0.6376    0.1828 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4790    2.1002   -0.5542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9609    1.3914   -0.1080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3285    0.2524   -1.7204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4545   -0.5633    1.1035 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0565   -1.4135   -0.3728 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7525    0.8370   -1.3467 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3535    1.5721    0.2166 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0591    0.4305    1.4101 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7272    1.2997    0.0228 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9000   -0.6112    0.0877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8834   -0.0483    1.0041 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  2  9  1  0
  9 10  2  0
  9 11  1  0
  1 12  1  0
  1 13  1  0
  2 14  1  6
  3 15  1  0
  3 16  1  0
  4 17  1  0
  4 18  1  0
  5 19  1  0
  5 20  1  0
  8 21  1  0
 11 22  1  0
M  END
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PDB for #<Metabolite:0x00007f922b796020>

HEADER    PROTEIN                                 22-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-20         0                                  
HETATM    1  C   UNK     0      -3.334   0.385   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.001  -0.385   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.667   0.385   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.667  -0.385   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.001   0.385   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.334  -0.385   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -3.334   1.925   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -4.668  -0.385   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       3.334  -1.925   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       4.668   0.385   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0      -2.001  -1.925   0.000  0.00  0.00           N+0
CONECT    1    2    7    8                                                  
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    9   10                                                  
CONECT    7    1                                                            
CONECT    8    1                                                            
CONECT    9    6                                                            
CONECT   10    6                                                            
CONECT   11    2                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   20    0
END
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3D PDB for #<Metabolite:0x00007f922b796020>

COMPND    HMDB0000510
HETATM    1  N1  UNL     1      -1.922   1.302  -0.040  1.00  0.00           N  
HETATM    2  C1  UNL     1      -1.560   0.025  -0.660  1.00  0.00           C  
HETATM    3  C2  UNL     1      -0.258  -0.439   0.010  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.754   0.632  -0.260  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.108   0.395   0.302  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.802  -0.805  -0.178  1.00  0.00           C  
HETATM    7  O1  UNL     1       2.265  -1.545  -1.025  1.00  0.00           O  
HETATM    8  O2  UNL     1       4.055  -1.135   0.297  1.00  0.00           O  
HETATM    9  C6  UNL     1      -2.649  -0.942  -0.480  1.00  0.00           C  
HETATM   10  O3  UNL     1      -2.515  -2.099  -0.947  1.00  0.00           O  
HETATM   11  O4  UNL     1      -3.823  -0.638   0.183  1.00  0.00           O  
HETATM   12  H1  UNL     1      -1.479   2.100  -0.554  1.00  0.00           H  
HETATM   13  H2  UNL     1      -2.961   1.391  -0.108  1.00  0.00           H  
HETATM   14  H3  UNL     1      -1.328   0.252  -1.720  1.00  0.00           H  
HETATM   15  H4  UNL     1      -0.455  -0.563   1.104  1.00  0.00           H  
HETATM   16  H5  UNL     1       0.057  -1.413  -0.373  1.00  0.00           H  
HETATM   17  H6  UNL     1       0.752   0.837  -1.347  1.00  0.00           H  
HETATM   18  H7  UNL     1       0.353   1.572   0.217  1.00  0.00           H  
HETATM   19  H8  UNL     1       2.059   0.431   1.410  1.00  0.00           H  
HETATM   20  H9  UNL     1       2.727   1.300   0.023  1.00  0.00           H  
HETATM   21  H10 UNL     1       4.900  -0.611   0.088  1.00  0.00           H  
HETATM   22  H11 UNL     1      -3.883  -0.048   1.004  1.00  0.00           H  
CONECT    1    2   12   13
CONECT    2    3    9   14
CONECT    3    4   15   16
CONECT    4    5   17   18
CONECT    5    6   19   20
CONECT    6    7    7    8
CONECT    8   21
CONECT    9   10   10   11
CONECT   11   22
END
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SMILES for #<Metabolite:0x00007f922b796020>

N[C@@H](CCCC(O)=O)C(O)=O
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INCHI for #<Metabolite:0x00007f922b796020>

InChI=1S/C6H11NO4/c7-4(6(10)11)2-1-3-5(8)9/h4H,1-3,7H2,(H,8,9)(H,10,11)/t4-/m0/s1
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Synonyms
ValueSource
(S)-2-Aminohexanedioic acidChEBI
L-2-AminoadipateChEBI
L-2-AminohexanedioateChEBI
L-alpha-AminoadipateChEBI
L-alpha-Aminoadipic acidChEBI
L-2-Aminoadipic acidKegg
(S)-2-AminohexanedioateGenerator
L-2-Aminohexanedioic acidGenerator
L-a-AminoadipateGenerator
L-a-Aminoadipic acidGenerator
L-Α-aminoadipateGenerator
L-Α-aminoadipic acidGenerator
AminoadipateGenerator
(2S)-2-Aminohexanedioic acidHMDB
(2S)-2-Azaniumyl-6-hydroxy-6-oxohexanoateHMDB
(S)-2-Aminoadipic acidHMDB
2-AminoadipateHMDB
2-Aminoadipic acidHMDB
2-Aminohexanedioic acidHMDB
L-Aminoadipic acidHMDB
alpha-Aminoadipic acidHMDB
Α-aminoadipic acidHMDB
Molecular FormulaC6H11NO4
Average Mass161.1558
Monoisotopic Mass161.068807845
IUPAC Name(2S)-2-aminohexanedioic acid
Traditional Nameaminoadipate
CAS Registry NumberNot Available
SMILES
N[C@@H](CCCC(O)=O)C(O)=O
InChI Identifier
InChI=1S/C6H11NO4/c7-4(6(10)11)2-1-3-5(8)9/h4H,1-3,7H2,(H,8,9)(H,10,11)/t4-/m0/s1
InChI KeyOYIFNHCXNCRBQI-BYPYZUCNSA-N